Polycyclic aromatic hydrocarbon compounds containing an S atom or S(═O)2 group in their basic structure

a technology of polycyclic aromatic hydrocarbons and aromatic hydrocarbons, applied in the direction of identification means, naphthalimide/phthalimide dyes, instruments, etc., can solve the problems of counterfeit or diverted products easily introduced into the supply chain, counterfeit or diverted documents are increasingly counterfeited around the world, and it is even more difficult to distinguish between fake documents and originals

Active Publication Date: 2015-06-23
SICPA HLDG SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In such case counterfeit or diverted products are easily introduced into the supply chain.
Further, secure documents such as currency, passports, or identity cards are increasingly counterfeit around the world.
This situation is a very critical issue for governments and society in general.
As reprographic technologies become more and more sophisticated, it becomes even more difficult to make a clear distinction between a fake document and the original.
However, a drawback of these compounds is their often unsatisfactorily low solubility or dispersibility in liquid media such as those which are useful in printing inks.
This low solubility / dispersibility limits the suitability of these compounds as colorants for liquid compositions in general.

Method used

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  • Polycyclic aromatic hydrocarbon compounds containing an S atom or S(═O)<sub>2 </sub>group in their basic structure
  • Polycyclic aromatic hydrocarbon compounds containing an S atom or S(═O)<sub>2 </sub>group in their basic structure
  • Polycyclic aromatic hydrocarbon compounds containing an S atom or S(═O)<sub>2 </sub>group in their basic structure

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examples

Preparation of 4,4′,4″-((2-(2,6-diisopropylphenyl)-1,3-dioxo-2,3-dihydro-1H-thioxantheno[2,1,9-def]isoquinoline-4,8,12-triyl)tris(oxy))tribenzenesulfonate. The orange solid of sodium 4,4′,4″-((2-(2,6-diisopropylphenyl)-1,3-dioxo-2,3-dihydro-1H-thioxantheno[2,1,9-def]isoquinoline-4,8,12-triyl)tris(oxy))tribenzenesulfonate

[0094]Compound 4,8,12-trichloro-2-(2,6-diisopropylphenyl)-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione (0.3 g), sodium 4-hydroxybenzenesulfonate (0.41 g) and anhydrous potassium carbonate (0.73 g) were added to 10 mL of N-methyl-2-pyrrolidinone (NMP). The solution was heated at 130° C. with good stirring within 4 hours. After boiling a further 4 hours, the solution was cooled at room temperature, after a minute the liquor was added to dichloromethane (100 ml) and the precipitate was filtered and dried at 60° C. to give a orange solid of sodium 4,4′,4″-((2-(2,6-diisopropylphenyl)-1,3-dioxo-2,3-dihydro-1H-thioxantheno[2,1,9-def]isoquinoline-4,8,12-triyl)tris(ox...

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Abstract

Polycyclic aromatic hydrocarbon compounds having an S atom or S(═O)2 moiety incorporated in their basic polycyclic structure that can have a nitrogen-containing heterocycloaliphatic group and / or a substituted or unsubstituted phenoxy group and / or a polymeric moiety bonded to the polycyclic structure and to compositions such as, e.g., printing inks which comprise these polycyclic aromatic hydrocarbons as colorants.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]The present application claims the benefit under 35 U.S.C. §119(e) of U.S. Provisional Application No. 61 / 563,381, filed Nov. 23, 2011 and claims priority under 35 U.S.C. §119 of International Patent Application No. PCT / EP2011 / 070869, filed Nov. 23, 2011. The entire disclosures of these applications are expressly incorporated by reference herein.BACKGROUND OF THE INVENTION[0002]1. Field of the Invention[0003]The present invention relates to novel polycyclic aromatic hydrocarbon compounds having an S atom or S(═O)2 moiety incorporated in their basic polycyclic structure that can have a nitrogen-containing heterocycloaliphatic group and / or a substituted or unsubstituted phenoxy group and / or a polymeric moiety bonded to the polycyclic structure and to compositions such as, e.g., printing inks which comprise these polycyclic aromatic hydrocarbons as colorants.[0004]2. Discussion of Background Information[0005]Counterfeiting and market diversi...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C09B57/08C07D495/16C09B5/62
CPCC09B57/08C09B5/62C07D495/16C07D221/18C07D495/06C08G83/00C09B57/14C09D11/32G09F3/02C08G8/28C09B57/00
Inventor PASQUIER, CECILEWYSS, PATRICK
Owner SICPA HLDG SA
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